How To Propose to Your Boyfriend

Surprise! Andy and I are engaged!

It just might be the reason for some of my sporadic silence over the past few weeks. Between the planning and the rollercoaster nervousness, there was a lot of unproductive time being wasted. But… it was totally worth it.

So why did I propose? Firstly: to screw gender norms.

Secondly: because my relationship with Andy has been a complicated one. It has involved me leaving the country twice, and me breaking his heart more than that. If we are going to commit to each other, then I wanted to be the one to initiate. I wanted to be the one who showed him just how much I want this. How far we’ve come from our one-night stand over three years ago.

I knew that a proposal from him was in the works for the upcoming months, but I never want him to feel like he has trapped me. So instead, I decided to trap him! Muahaha!

For those who are curious, this is how I proposed to my boyfriend.

How to Propose to Your Boyfriend

1. Decide

Once the idea of proposing had crossed my mind, I couldn’t get rid of it. I knew in my core that this was the right idea. Not only did I want to spend my life adventuring with Andy but I just knew it had to be me doing the proposing. I messaged my sister to ask her if I was crazy. Her response: “I think it is perfect for your relationship”. Please note that my sister is also super feminist (yay!).

2. Ask Permission

As much as a female-to-male proposal is untraditional, there are still some traditions that need respecting: I went and asked his parents. I did this to be polite, but also to let them know that this was happening. I wasn’t really expecting them to say “no” but it was still terrifying to ask. I decided to ask them before telling my own parents, just in case they didn’t give permission. Thankfully, I didn’t have to deal with that because they both said yes! They were shocked at the role-reversal but loved that I was committing to their son after so many years of being a flake.

3. Tell The Parents

I’m not super close to my parents, but I figured that they should probably know beforehand. Traditionally, they would have been asked permission from Andy and I didn’t really want to take that away from them. I knew my mom would want all the details and my dad would need time to accept the gender role-reversal. It went exactly as I had expected.

4. Buy The Gift

I knew there had to be some kind of gift, something to symbolize the moment. Traditionally, a diamond ring is given, but I didn’t think Andy would be too fond of that. I could have bought him a watch, but those go out of style. He doesn’t wear any jewelry so there weren’t many options left. I wanted something to be timeless and unique. While shopping, I came across the perfect gift: a pocket watch. It was a one-of-a-kind gift that would last a lifetime and able to be passed down to any future children. It was also something he could wear during our wedding ceremony.

5. Plan The Proposal

Now that I had informed all the appropriate people as to what I was planning on doing, I had to come up with a way to make it special. I knew Andy wouldn’t like anything public, but I also knew how important his friends are to him. Our relationship is unconventional, so I didn’t want to go down the typical “dinner and propose” route. That might work for some, but it just wouldn’t feel right for us.

I decided to ask all of his friends to send me a video clip of them saying something they love about Andy. I then put together a video compilation for him to watch. Of course, the last video clip was going to me stating the reasons why I love Andy so much.

At the end of the video, I would ask him to marry me and give him the gift.

6. Plan the Day

Once I had told all of his friends to send me a video, I knew it was only a matter of time before someone ruined the surprise. His friends had no idea what it was for, and that made it a dangerous secret. All I needed was a friend to mention the video and it was over. So I planned a dinner with Andy. Actually, I made him agree to take me out to dinner (don’t worry, in the end I was the one who paid). I needed him to be home and ready to go out for the night. I planned the dinner right after a day he was going to be in meetings, so I would have time to put the video together when he was out of the house.

7. Write The Speech

At the end of the video, I was going to profess my eternal love for Andy. I decided to list the reasons why I love him and then take it a step further and write a set of vows. I wanted to make him laugh and cry simultaneously, and most importantly I wanted to make sure he knew what was going on! I wrote my speech and then recorded it about 20 times until I had it just right.

8. Propose

Andy was busy during the day so I had time to set everything up. The video was done, the gift was hidden in the coffee table, and I put on one of his favourite outfits. The moment he got home, I couldn’t wait any longer. I sat him down on the couch and showed him the video compilation. Before I could even finish the sentence “Will you marry me?” he said YES! It was followed by a lot of kisses and wiping away happy tears.

9. Celebrate

We proceeded to call our family and closest friends (mine were on standby waiting to hear his response). His friends were over-the-moon for us and so amazed that they had been made part of the proposal. We then went for dinner at the same restaurant where we had our second date. And then had sex in the park where we had our first public sexcapade on our third date (but none of you are surprised, right?).

We aren’t planning the wedding just yet. We don’t even know if we want to have a formal ceremony or if we will just head over to city hall to sign papers. We’re not going to plan it for a while and I am totally okay with that. The engagement means more to me than a wedding. It means that through thick and thin, we have already committed to each other. Through all the highs and lows of daily life, I have a partner by my side. We already live together so it doesn’t technically change anything, but I am super proud to call Andy my fiancé.

We were so excited to share this news with all of you! Thank you for reading!